Sales Executive / New Business Sales Representative (Remote)

About Us: Upswing is a mission-driven company partnering with colleges and universities to improve nontraditional student outcomes. Over 28% of students using Upswing are working while in college, and 43% are Hispanic or Black, with many being first-generation students. Our platform is cost-free for students, as the schools enlist our help to support their students. We're seeking individuals passionate about education and equal student resources to join our team!

We currently partner with over 70 colleges across the country, helping over 700,000 students succeed throughout college. You'll work with a motivated, intelligent, and fun team at Upswing, all working toward the same mission of student success and retention.

As a mission-driven organization, we strive to build a community inside Upswing where we live our values to help our students grow and thrive. Our values reflect why we do what we do and how we plan to do it. We hope to build a team that embodies these values so we can all grow together.

Celebrate Concrete Roses

Dare to Fly First

Choose the Harder Right over the Easier Wrong

Overview: Upswing is expanding and looking to hire two Sales Executives / New Business Sales Representatives to drive our growth in the Central and East territories. Although remote, we are open to candidates living anywhere in the US.

We seek savvy, personable, driven, and goal-oriented salespeople with experience developing and onboarding new clients in the Higher Education market. The ideal candidate will have over 3 years of enterprise sales experience in EdTech, a track record of goal attainment, an autonomous working style, and be proficient in using CRMs to track their progress.

Day in the Life:

Ownership: Be the "CEO" of your own territory. Manage the full sales cycle, from prospecting and gathering information to calling departments, securing demos, and efficiently moving prospects through the pipeline to close.

Industry Expertise: Utilize your knowledge of higher education institutions to reach out to and connect with prospective schools within your region.

Travel: Attend around 4 conferences per year and participate in a few on-campus meeting days.

Collaboration: Work with various Upswing team members to understand the industry better and ensure we provide the best information to our prospects.

Passion for Technology: Be passionate about leveraging technology to improve student outcomes.

Strategic Communication: Communicate with the VP of Revenue on pipelines to strategize growth.

Team Integration: Connect and collaborate with a team of hardworking, passionate professionals focused on improving access to education for all.

Skills and Qualifications:

Experience: Minimum of 3 years in enterprise sales, preferably in the higher education space, with a strong track record of goal attainment.

Industry Knowledge: Familiar with higher education budget cycles, grants, and organizational hierarchy.

Prospecting Success: Proven successful prospecting track record, committed to maintaining a robust pipeline.

Hunter Mentality: Ability to build and nurture client relationships with a hunter mentality.

Communication Skills: Clear and concise elevator pitch delivery of the services you're selling.


Comfortable with Outreach: Comfortable making phone calls, leading demos, and meeting with clients both in person and virtually.

Self-Motivation: Self-motivated "can-do" attitude, ready to contribute to our growing sales organization.

Relationship Building: Excellent relationship-building skills with a sustained focus on customer needs throughout the sales process.

Organizational Skills: Highly organized, able to juggle multiple different projects with competing timelines, and proficient with various CRMs and able to keep things organized.

Sales Model Familiarity: Familiar with the "predictable revenue" sales model and work well in a team-based setting.

Upswing Benefits and Perks:

Salary: Base salary between $80k-95k (DOE)

Commission: Variable commission of $45 - 60K at goal, uncapped with unlimited earning potential

Flexible Start Date: Based on candidate availability

Health Coverage: Health, dental, and vision coverage

Retirement Plan: 401k program

PTO: Unlimited PTO and flexible working hours

Remote Work: Fully remote organization

Team Culture: Mission-driven, passionate coworkers with an awesome remote team culture

How to Apply: Interested candidates can apply directly online at upswing.io/careers.

Join us at Upswing and help us transform the future of higher education!